Trifluoroacetic acid → HCID 49865936, compound

HRID 1895037Notes

Reaction equation

HRID 1895037 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([C:19]3([CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22][CH2:21][N:20]3C(OC(C)(C)C)=O)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([C:19]3([CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22][CH2:21][NH:20]3)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666873605-(1-Tert-butoxycarbonyl-2-propyl-pyrrolidine-2-carbonyl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 49865936HCID 49865936, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(1-tert-butoxycarbonyl-2-propyl-pyrrolidine-2-carbonyl)-indole-1-carboxylic acid tert-butyl ester (0.132 g, 0.289 mmol) in DCM (3 mL) at 20° C. under nitrogen was added TFA (1 mL). After 14 hours the reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with DCM. The combined organic phases were concentrated in vacuo then purified by chromatography (silica, 0 to 30% MeOH in DCM) to furnish (1H-indol-5-yl)-(2-propyl-pyrrolidin-2-yl)-methanone (0.053 g, 0.207 mmol, 72%) as a beige foam, MS=257 [M+H]+.

Workup

  1. customAfter 14 hours the reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with DCM
  3. concentrationThe combined organic phases were concentrated in vacuo
  4. customthen purified by chromatography (silica, 0 to 30% MeOH in DCM)

Sources & evidence

ORD record
ord-369e7aedcee34d9b91123faaa8fcc781
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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